Book Holiday Homes in Upwey

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Featured Holiday Homes in Upwey

Edwardian House in the Heart of Weymouth 200m from Sandy Beach by the Sea

Edwardian House in the Heart of Weymouth 200m from Sandy Beach by the Sea

Weymouth
With a stay at this vacation home in Weymouth, you'll be by the sea, just a 1-minute walk from Weymouth Bay and 6 minutes by foot from Greenhill Beach.
Edwardian House in the Heart of Weymouth 200m from Sandy Beach by the Sea
Private detached cottage to rent on Chesil Beach

Private detached cottage to rent on Chesil Beach

Abbotsbury
When you a stay at this vacation home in Weymouth, you'll be by the ocean, just steps from Dorset and East Devon Coast and Chesil Beach.
Private detached cottage to rent on Chesil Beach
Historical, Characterful, Converted Old School House

Historical, Characterful, Converted Old School House

Lower Bockhampton
Located in Dorchester, this vacation home is within a 5-minute drive of Kingston Maurward Park and Gardens and Dorset Teddy Bear Museum.
Historical, Characterful, Converted Old School House
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Host & Stay | Clearmount Cottage

Host & Stay | Clearmount Cottage

Weymouth
With a stay at this vacation home in Weymouth, you'll be by the sea, just a 1-minute walk from Weymouth Bay and 7 minutes by foot from Sandsfoot Castle.
Host & Stay | Clearmount Cottage
Nothe House - Exclusive home, Weymouth Harbour

Nothe House - Exclusive home, Weymouth Harbour

Weymouth
When you a stay at this vacation home in Weymouth, you'll be on the waterfront, just steps from Weymouth Bay and Weymouth Harbour.
Nothe House - Exclusive home, Weymouth Harbour
Eclectic Dorset Country House, Hot Tub, Pool Table, Movie Room,12 guests & pets

Eclectic Dorset Country House, Hot Tub, Pool Table, Movie Room,12 guests & pets

Mapperton
Located in Blandford Forum, this vacation home is within a 10-minute drive of White Mill and Skirmish Dorset.
Eclectic Dorset Country House, Hot Tub, Pool Table, Movie Room,12 guests & pets
Ideal quiet beach location for walking/cycling/watersports & Jurassic Coast

Ideal quiet beach location for walking/cycling/watersports & Jurassic Coast

Wyke Regis
With a stay at this vacation home in Weymouth, you'll be on the waterfront, just a 1-minute walk from Weymouth Bay and 6 minutes by foot from South West Coast ...
Ideal quiet beach location for walking/cycling/watersports & Jurassic Coast
Luxury Detached House and Grounds, also benefits from full disabled facilities.

Luxury Detached House and Grounds, also benefits from full disabled facilities.

Whitcombe
Located in Dorchester, this vacation home is in a rural location, within a 5-minute drive of Max Gate and Hardy Literary Locations.
Luxury Detached House and Grounds, also benefits from full disabled facilities.
 Beautiful, family friendly Cottage with sea views of Chesil Beach

Beautiful, family friendly Cottage with sea views of Chesil Beach

Fortuneswell
When you a stay at this vacation home in Portland, you'll be by the sea, within a 5-minute walk of Royal Manor Theatre and Dorset and East Devon Coast.
Beautiful, family friendly Cottage with sea views of Chesil Beach
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Upwey Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Upwey vacation homes are the perfect way for you to wing it.

Holiday houses in Upwey let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Upwey in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Upwey adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Upwey with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Upwey vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Upwey Holiday Homes essential information

Accommodation
186 Holiday Homes
Lowest Price
AU$120
Highest Price
AU$135
Popular accommodation
Edwardian House in the Heart of Weymouth 200m from Sandy Beach by the Sea, Private detached cottage to rent on Chesil Beach, Historical, Characterful, Converted Old School House, Host & Stay | Clearmount Cottage, Nothe House - Exclusive home, Weymouth Harbour, Eclectic Dorset Country House, Hot Tub, Pool Table, Movie Room,12 guests & pets, Ideal quiet beach location for walking/cycling/watersports & Jurassic Coast , Luxury Detached House and Grounds, also benefits from full disabled facilities., Beautiful, family friendly Cottage with sea views of Chesil Beach

Top trending hotels in Upwey

Best Western Weymouth Hotel Rembrandt

Best Western Weymouth Hotel Rembrandt

3 out of 5
12-18 Dorchester Road, Weymouth, England
Fully refundableReserve now, pay when you stay
The price is AU$135 per night from 22 Dec to 23 Dec
AU$135
includes taxes & fees
22 Dec - 23 Dec
With a stay at Best Western Weymouth Hotel Rembrandt in Weymouth, you'll be by the sea, just a 4-minute walk from Weymouth Bay and 6 minutes by foot from Greenhill ...
Best Western Weymouth Hotel Rembrandt
Fairhaven Hotel

Fairhaven Hotel

2.5 out of 5
Fairhaven Hotel, 37 Esplanade, Weymouth, England
Fully refundableReserve now, pay when you stay
The price is AU$120 per night from 23 Dec to 24 Dec
AU$120
includes taxes & fees
23 Dec - 24 Dec
Located in Weymouth, Fairhaven Hotel is near the beach, within a 5-minute walk of Weymouth Bay and Weymouth Ferry Terminal.
Fairhaven Hotel
The Jubilee Hotel East- with Spa Facilities

The Jubilee Hotel East- with Spa Facilities

3 out of 5
143-146 The Esplanade, Weymouth, England
Fully refundableReserve now, pay when you stay
The price is AU$126 per night from 19 Dec to 20 Dec
AU$126
includes taxes & fees
19 Dec - 20 Dec
A stay at The Jubilee Hotel East- with Spa Facilities places you in the heart of Weymouth, steps from Weymouth Bay and 4 minutes by foot from Jubilee Clock Tower ...
The Jubilee Hotel East- with Spa Facilities
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Crown Hotel

Crown Hotel

3 out of 5
West Street, Blandford, Forum, Nr Wareham, Blandford Forum, England
Fully refundableReserve now, pay when you stay
The price is AU$130 per night from 12 Jan to 13 Jan
AU$130
includes taxes & fees
12 Jan - 13 Jan 2025
With a stay at Crown Hotel in Blandford Forum, you'll be within a 5-minute walk of Blandford Forum Town Museum and Dorset Area of Outstanding Natural ...
Crown Hotel
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.